1-Aminocyclobutanecarboxylic acid Chemical Properties

Melting point:

261 °C (dec.)(lit.)

Boiling point:

241.1±23.0 °C(Predicted)

Density 

1.290±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.38±0.20(Predicted)

form 

Powder

color 

White

Water Solubility 

Soluble to 100 mM in water.

InChI

InChI=1S/C5H9NO2/c6-5(4(7)8)2-1-3-5/h1-3,6H2,(H,7,8)

InChIKey

FVTVMQPGKVHSEY-UHFFFAOYSA-N

SMILES

C1(N)(C(O)=O)CCC1

CAS DataBase Reference

22264-50-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

GU1336000

HazardClass 

IRRITANT

HS Code 

2922498590

MSDS

• Language:English Provider:SigmaAldrich

1-Aminocyclobutanecarboxylic acid Usage And Synthesis

Uses

ACBC is an NMDA receptor antagonist acting at the glycine site. It acts as an agonist being an analog of glycine at the NMDA-glycine receptor site. This affects the signal transmission in the CNS.

Uses

1-Aminocyclobutanecarboxylic acid acts as an agonist being an analog of glycine at the NMDA-glycine receptor site. This affects the signal transmission in the CNS.

Definition

ChEBI: 1-AMINOCYCLOBUTANE CARBOXYLIC ACID is a L-alpha-amino acid.

reaction suitability

reaction type: solution phase peptide synthesis

Biological Activity

NMDA receptor antagonist acting at the glycine site.

Synthesis

1. 1-carbamoyl-cyclobutanecarboxylic acid (1.43 g, 10.0 mmol, 1 eq.) was dissolved in a water-ice bath under nitrogen protection and 1N aqueous NaOH solution (10 mL, 10.0 mmol, 1 eq.) was added slowly. 2. NaOCl solution (10-13% solution, 9.0 mL, ~15.0 mmol, 1.5 eq.) was added slowly and the reaction mixture was stirred for 1 hour at 5 °C. 3. 10N NaOH solution (2.0 mL, 20 mmol, 2 eq.) was added slowly, keeping the reaction temperature below 20 °C and stirred at 15-25 °C for 3 h. The reaction was monitored by LC-MS. The completion of the reaction was monitored by LC-MS. 4. Quench the reaction with an aqueous solution (3 mL) of Na2S2O3-3H2O (2.48 g, 10 mmol, 1 eq.) at 15 °C and continue stirring for 1 hour. 5. Neutralize the reaction mixture with 12N HCl aqueous solution to pH=7.0. 6. Volatiles were removed by azeotropic distillation with toluene under reduced pressure to give about 9 g of white solid. 7. The solid was extracted with methanol (3 x 30 mL) and 2.0 g of crude product was obtained after evaporation of methanol. 8. By 1H NMR analysis, it was determined that the solid contained 0.81 g of the target product, 1-aminocyclobutanecarboxylic acid (70% yield), and the rest were inorganic salts. 9. Comparison of 1H and 13C NMR data confirmed that the structure of the product was consistent with the standard sample provided by Sumitomo Chemical, Inc.

storage

Room temperature

References

[1] Patent: WO2005/19158, 2005, A1. Location in patent: Page/Page column 18

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